State of Play

Ben Huffman built a company everyone called stupid. Until more than 1M people were using it.

In this episode of State of Play, the Contra's design founder shares how he went from college dropout to building a new path for creative independence.

We get real about the pain cave: that brutal, lonely gap between your vision and the world’s doubt, and how to keep going when no one believes in you.

If you’re building something and feel like no one gets it, this one’s for you.

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CHAPTERS:
00:00 - Why investors laughed
02:04 - Getting your first client
03:03 - Trust issues with platforms
04:32 - Building with 0% commission
05:40 - The sting of rejection
07:36 - Near burnout and losing it all
08:57 - How Contra makes money
10:02 - A 20-year-old earns $50k
12:24 - $50k/month playbook
13:40 - Why it’s a great time to be creative
14:25 - The “Hollywood model” shift

SPECIAL THANKS:
- Sam Chapman: https://x.com/editedbysam
- Mapal Berenson: https://www.youtube.com/@mapal
- Bernabe Bolanos: https://www.youtube.com/@BernabeBolanos
- Adam Stewart: https://www.instagram.com/adnastu/
- Tom Fox: https://catalog.tomfox.site/

ABOUT TOMMY GEOCO
I spent 15+ years in tech and design. Former military. Father of five. Now building Internet Enjoyers, a weird little media + product studio rediscovering soul in creative tech. This show is how I stay sane and spotlight the outsiders reshaping how we enjoy the internet.

ABOUT STATE OF PLAY
A narrative podcast about building things that matter told through deep conversations with designers and builders. 

LINKS
UX Tools Newsletter: https://uxtools.co
Follow Ben: https://x.com/_BenHQ
Check out Contra: https://contra.com

What is State of Play?

Host Tommy Geoco discovers what fuels the internet's most interesting designers and builders.

S1 0:00
I'm about to show you a founder who every investor said was building

S1 0:04
the stupidest idea they'd ever heard.

S1 0:07
This is what they told him. No one believed in it.

S1 0:09
They're like, this is dumb. This is the worst idea ever.

S2 0:12
This is so stupid. How are you gonna make money?

S2 0:14
I just remember, like, feeling

S2 0:15
so like the wind just was taken out of my sails.

S2 0:18
What they're really. Saying is, like, I don't believe in you.

S1 0:20
I don't think you could do this.

S1 0:21
I don't think you can build this. This shouldn't exist.

S1 0:24
They laughed at him, literally laughed.

S1 0:26
But here's what they didn't know that increasing the amount freelancers

S1 0:29
earn would instantly make contra a creator's home.

S1 0:33
Over the next 30 minutes, you're going to learn why.

S1 0:34
Betting against the obvious might be the smartest thing you ever do,

S1 0:38
and why I'm doing the same thing right now.

S1 0:41
Let me crack into that, because that's really interesting.

S2 0:44
I'm curious what your take on that is.

S1 0:47
Ben Huffman isn't supposed to be here.

S1 0:49
No degree, no connections, no Silicon Valley pedigree like me.

S1 0:53
We were just two kids who found our future on the early internet.

S1 0:56
This is where we both started.

S1 0:57
I built my first. Computer when I was 13 from components and even younger

S2 1:01
we had a family computer, but it was in my parents room. I couldn't really use it.

S2 1:04
I was like, oh man, I really want this PC.

S2 1:06
So I'd save up money, like doing chores.

S2 1:08
I think it might have been like 2 or $300 for all the components

S2 1:11
to basically build my first computer, I built it.

S2 1:13
I immediately fell in love with the internet, and I'm from rural South Carolina.

S2 1:17
There's not a lot to do there.

S2 1:18
It's beautiful, but not a lot going on for

S2 1:21
someone who's young, has a lot of ideas, a lot of energy.

S2 1:24
And when I was 19, about to turn 20,

S2 1:27
I dropped out of school and moved up to New York.

S2 1:30
I was a college dropout. So there's a lot of imposter syndrome there.

S2 1:33
A lot of the people I would interact with, they were all working

S2 1:36
at, like cool tech companies or like Facebook or whatever.

S2 1:40
And I just remember thinking like, wow, I could never do that.

S2 1:42
I don't have a degree, no one to hire me.

S2 1:45
There's nothing on my resume.

S2 1:46
I'm just good with computers.

S1 1:48
I remember my first website, 800 pixels wide borders,

S1 1:51
that I spliced out of a cracked version of Photoshop, cringe

S1 1:55
poetry, and blog entries.

S1 1:57
At 13, I didn't know what I was doing and I loved it.

S1 2:00
Then something changed.

S1 2:02
There was a moment that rewired everything.

S2 2:04
I remember when I got my first freelance project.

S2 2:08
Everything changed. Like for the first time,

S2 2:10
I felt like someone valued my opinion.

S2 2:12
Someone recognized my skills and were like, whoa, like, you can actually help me.

S2 2:16
And that was so validating because, you know,

S2 2:19
having that moment to say, like, hey, I'm the expert, I can help.

S2 2:22
I have authority here. That was big.

S1 2:24
You took me back to when I first started in the field.

S1 2:27
And I think I think it was Elance.

S1 2:29
I left the military and I was just sprinting.

S1 2:32
I had already had four children at that point,

S1 2:34
and I was sprinting to upskill myself

S1 2:37
and be valuable enough to charge rates.

S1 2:39
I didn't know how to sell, and it was Elance,

S1 2:41
and I was like, just picking at the lowest quality jobs

S1 2:44
I could get for $500 for like a WordPress website.

S1 2:48
And it was it was like, I have to take them off platform immediately,

S1 2:51
and it just felt very cold and calculated.

S1 2:54
That first client that believes in you

S1 2:56
feels like oxygen to somebody who's drowning,

S1 2:59
but the platforms at the time

S1 3:01
felt like they were bleeding us dry.

S2 3:03
Like if you're using a platform that has commission fees,

S2 3:06
it already like, puts us at odds with each other.

S2 3:08
The more you pay me, the more the platform earns.

S2 3:12
And so you're kind of like as a platform trying to, like,

S2 3:14
make me pay more.

S2 3:15
Like, that's kind of weird.

S2 3:16
And then for me, I'm like trying to get you off

S2 3:18
this platform as fast as possible.

S2 3:20
So I'm acting sketchy. I'm like, hey, Tommy, please.

S2 3:22
Like, I don't want to pay this 20%.

S2 3:24
Like, can we just get off? I need to like, pay my bills and shit.

S2 3:27
And so, like, that creates this weird kind of divide

S2 3:30
that kind of takes away the humanity of the relationship. Right.

S2 3:32
And so I think more people are going to be like me

S2 3:36
where they're young, they're skilled, they're gonna need to enter the workforce,

S2 3:39
they're going to need to get experience,

S2 3:41
and they need to come into an ecosystem that actually has a lot of incentives

S2 3:45
with the outcome that they're trying to achieve. They're trying to get better.

S2 3:47
They're trying to prove themselves. They're trying to get their footing. But let's back up.

S1 3:51
Where did this all begin?

S2 3:52
There was like Newegg.

S2 3:53
There was all these other like, sites

S2 3:55
where you could, like, nerd out about like graphics cards or motherboards,

S2 3:59
and there's tons of forums that kind of supported those.

S2 4:01
I loved torrent sites where I could basically crack

S2 4:05
the latest version or download the latest keygen

S2 4:07
for whatever software I wanted to use.

S2 4:09
I loved Themeforest. Funny enough.

S2 4:11
I thought Themeforest was amazing to get get started

S2 4:14
with like a WordPress template or a bootstrap template or whatever.

S2 4:16
Like you could buy code, you could buy video graphics, buy like After Effects templates.

S2 4:21
I thought that was the coolest thing.

S2 4:24
A lot of a lot of talking.

S2 4:26
I'm sure a lot of people got their their start that way too.

S1 4:29
These weren't just websites, there were communities and real ones.

S1 4:32
But in 2019, Ben had an idea so simple it was radical.

S1 4:36
What if freelancers kept 100% of what they made?

S2 4:41
So in the beginning, when we were starting contra, I had that feeling.

S2 4:45
I was like, wow, this is the greatest idea ever.

S2 4:47
Like, of course, like no one wants to pay commission fees.

S2 4:50
Of course, the creative industry is going to get behind this.

S2 4:53
Of course, it's so easy to build payments

S2 4:55
and something that people actually want to use.

S2 4:57
And all of these things like this is

S2 4:59
this is a no brainer, Commissioner. Free. This is obvious.

S2 5:01
I remember when we first went out to raise money for contra.

S2 5:05
Everyone was like, this is the worst idea ever.

S2 5:07
They're like, this is so stupid.

S2 5:09
They're like, how are you gonna make money?

S2 5:11
Why would people want to join a website?

S2 5:14
Everyone just wants like, the best people just have their own portfolio

S2 5:17
and they just want to get leads from referrals.

S2 5:19
And then the worst people are going to be on like,

S2 5:21
Fiver and Upwork, and they don't care about paying commission fees.

S2 5:24
And I was like, I was like, look, that's

S2 5:25
probably not what the future is going to be.

S2 5:27
There's going to be all these interconnected systems.

S2 5:28
Now, you see, X is this amazing ecosystem

S2 5:31
for creatives and designers that didn't really exist back then.

S2 5:34
And I just remember, like, feeling

S2 5:35
so like the wind just was taken out of my sails

S2 5:37
like no one believed in it. They're like, this is dope.

S2 5:40
And it was what they were really saying is like, I don't believe in you.

S2 5:43
I don't think you could do this, and I don't think you can build this.

S2 5:46
And this didn't exist.

S2 5:48
And that was kind of like my first experience,

S2 5:51
like trying to get other people to believe in contra.

S2 5:54
And because it's a commission free model,

S2 5:56
like, we didn't really have

S2 5:57
a lot of ways to make money in the early days, so we couldn't

S2 5:60
really just bootstrap the revenue.

S2 6:02
So I had to just plow all my savings into it and just keep going.

S2 6:05
But like, that was one of the first examples of the pain cave.

S2 6:08
When you have all this excitement and you're like, wow,

S2 6:10
you're like psyching yourself up every day and then the world just doesn't,

S2 6:14
you know, agree.

S1 6:16
I know this feeling intimately.

S1 6:18
I feel like I've lived a lot of my life in the pain cave,

S1 6:21
a lot of ideas that unfortunately didn't make it out of the pain cave.

S1 6:26
How do you not take it personal

S1 6:28
when someone doesn't see your vision

S1 6:30
and you're in that place and it's so painful?

S1 6:34
I think. Of course you take it personally, right?

S2 6:36
Like it's very personal.

S2 6:38
You put your blood, sweat and tears into something

S2 6:41
and you put yourself out there saying like,

S2 6:44
hey, what do you think about this?

S2 6:45
And you get rejected

S2 6:48
and it hurts and it's very personal.

S2 6:50
And like, inside you're like, ah,

S2 6:52
like, I'm going to show this person, like,

S2 6:53
I'm never going to let this person invest.

S2 6:55
I'm never going to let this person, you know, even like it.

S2 6:58
Just all the thoughts like swirling your in your head. Right.

S2 7:01
When you take it personally, there's no way not to.

S2 7:03
And I think over time we realize that all the good ideas, they're not obvious?

S2 7:07
Anything that's good that's worth doing

S2 7:10
is probably not that obvious to a ton of people.

S2 7:12
And if it was, then it's probably not the best idea,

S2 7:14
because there'd be tons of competition

S2 7:16
and it'd be super saturated and everyone would be trying to do it.

S2 7:18
I just need to keep going and see if I can prove them wrong.

S2 7:21
And so I don't know.

S2 7:22
I've never found a good way

S2 7:24
to not get emotional and take it personally.

S2 7:26
I'm curious, like what your take on

S2 7:28
that is, because I could probably use some advice there.

S1 7:30
I can't give you good advice because I take it personal.

S1 7:32
Every single time. I need to tell you about the moment everything almost ended.

S1 7:36
It's 2015, the first ever Twitch conference.

S1 7:39
We land in San Francisco and I get a phone call.

S1 7:42
It's my wife and she says our only family vehicle,

S1 7:45
the one we use to transport our four kids, needs a new engine.

S1 7:48
I'm in the Marriott hotel lobby crying,

S1 7:51
trying to figure out how I'm going to tell my co-founders

S1 7:54
that I need to go back home to find more client work and ASAP.

S1 7:58
My co-founder said, we're already here.

S1 8:01
Let's make the most of it.

S1 8:02
48 hours later, we have two acquisition offers.

S1 8:06
Four weeks later, we're moving to San Francisco,

S1 8:09
but the first version was kind of confusing and unintuitive.

S1 8:13
People weren't willing to leave their complicated setups

S1 8:16
for our different, but still complicated tool.

S1 8:18
I thought I got it all wrong and I nearly threw in the towel.

S1 8:21
But here's the thing about selling your dream.

S2 8:23
It's crazy because when we were commission free

S2 8:26
and we had no way of monetizing, it actually hurt our credibility.

S2 8:29
People were like, okay, this company's not going to survive.

S2 8:32
Like, why am I going to put any time into this?

S2 8:34
Like, you're not charging anything.

S2 8:35
It's free. Like, what's going to happen? I made the same bet.

S1 8:38
I refused to charge creators,

S1 8:40
but then I ran out of money and I had to sell.

S1 8:43
And that decision still haunts me.

S1 8:45
I spent years trying to build something to help creators make money.

S1 8:48
Then I sold it because I couldn't figure out

S1 8:50
how to make money without feeling like I'd betrayed them.

S1 8:53
How do you build something sustainable

S1 8:55
without losing your love for the game?

S2 8:57
But now we have Culture Pro.

S2 8:59
We have partner network subscriptions, we have an ad network,

S2 9:02
we have contract fees for clients,

S2 9:05
we have subscriptions for companies who are hiring.

S2 9:07
And we have something Actually, I'm going to leak it to you

S2 9:10
for your for your Friday leaks. That's right.

S1 9:12
UX tools is a newsletter I write for almost 100,000 readers.

S1 9:16
I dig into the latest design tools

S1 9:18
and how some of the best people and teams are creating software.

S1 9:22
Check it out at UX tools, and if you like following stories

S1 9:25
like mine or hearing from people like Ben,

S1 9:28
please subscribe to the designer Tom YouTube channel where I drop

S1 9:31
new episodes of this podcast and videos like it every week.

S1 9:35
Your support right now is huge.

S2 9:37
When you try to monetize with value ads

S2 9:41
versus being a pure middleman versus being value extracting,

S2 9:44
we try to only monetize via value

S2 9:46
additive features or products or whatever it is,

S2 9:49
and so you'll probably see a discount for framer on contract.

S2 9:52
You'll probably see a discount for a design school.

S2 9:55
Or you might see a discount for like your favorite animation tool.

S2 9:58
And in a lot of ways, I'm building contour for the younger version of me.

S2 10:02
And I see these people all the time.

S2 10:04
I remember I saw this one tweet from one of our users named Luca.

S2 10:07
He was like, hey, I just got my $50,000 dollars earnings badge on contra.

S2 10:11
Hopefully I'll hit 100 K before I turn 21

S2 10:14
and I'm like, Holy shit,

S2 10:15
that's amazing. It's working right?

S2 10:17
And so Luca can now find his way in the world

S2 10:21
in a way that I wish I could have when I was his age.

S1 10:23
After the acquisition, after corporate life,

S1 10:26
I was laid off and I did the only thing I could think of.

S1 10:29
I started a slide group and invited for my friends not to farm likes

S1 10:32
and not to sell something, but to be able to wake up

S1 10:35
and have people to work alongside of.

S1 10:38
This community gave me clients.

S1 10:40
It gave me Sally and Femke.

S1 10:43
It gave me config events with Jesse and Sorin.

S1 10:46
It gave me a place to be human when everything else felt impossible.

S1 10:49
The reality I'm learning is that community

S1 10:51
isn't just something you find, it's something you build.

S2 10:54
That's how contra started.

S2 10:55
We had a slack community

S2 10:58
for independent creatives.

S2 11:00
You had like 10,000 people in there at peak.

S2 11:02
Yeah, it's really interesting to see kind of

S2 11:05
some of our beta users

S2 11:07
already develop friendships, meet up in real life.

S2 11:10
Start podcast together.

S2 11:12
Start creating content together.

S2 11:14
Teaching each other like framer tricks.

S2 11:16
Teaching each other like content tricks.

S1 11:19
It seems like we've never had more communities spinning up for,

S1 11:23
you know, individual creators and companies,

S1 11:27
but everything seems so.

S1 11:29
It has to be a marketing funnel.

S1 11:30
It's fabricated.

S1 11:32
Like it doesn't seem authentic, like those

S1 11:35
like the a form on like Tom's Hardware way back in the day,

S1 11:39
or even like the forms on those torrent websites.

S1 11:42
There was real relationship building happening,

S1 11:45
and it seems like that's hard to come by these days,

S1 11:48
but it shouldn't be because we're right in front of each other.

S2 11:51
How do you not create an echo chamber?

S2 11:52
Right? With these like algorithms,

S2 11:54
how do you not just give someone more of what they like?

S2 11:56
How do they even discover something new and develop new taste? Right.

S2 11:59
Even seeing this with Spotify, like they have, like

S2 12:01
there's like these magic recommenders, right?

S2 12:04
Like, if you have a playlist, you can, like turn on the AI playlist creator

S2 12:08
and it'll just find you music

S2 12:09
that's complementary to the stuff security lake, but does not create an echo chamber.

S2 12:13
Are you actually going to be able to discover something new?

S2 12:15
I don't know, but that's the general trend of the internet today.

S2 12:17
And so I don't know what the the answer is,

S2 12:19
but it's a hard problem. And if someone solves it.

S1 12:21
They'll get out of the pain. Cave.

S2 12:22
Yeah. Want to know what's possible?

S1 12:24
Now? Let me tell you about a 19 year old kid named Mark.

S2 12:27
There's just one contra user who operates his agency.

S2 12:31
I actually just met him in San Francisco. His name is Mark.

S2 12:33
You probably have seen him on Twitter, but he's like 19 from Kazakhstan.

S2 12:38
He's pulling in like 50 K a month.

S2 12:40
I'm not even joking. This is all through X though.

S2 12:41
He's just like has this like formula where he's he's like, he's 19 years old.

S2 12:45
He got his visa to the US because of stripe sessions.

S2 12:48
So he basically stripe wrote him recommendations letter

S2 12:51
and then he was able to get his visa.

S2 12:53
And so like now he's in the US.

S2 12:55
When you meet someone who's 19

S2 12:56
you're probably like, I don't know, can you actually do good work?

S2 12:58
He basically made a free

S2 13:00
like kind of jitter animation

S2 13:02
for the bolt hackathon.

S2 13:04
And then the bolt team reached out to him

S2 13:07
saying like, well, he just posted it on Twitter. He just posted on X.

S2 13:11
He's like, killer work using this cool new tool for free for this company.

S2 13:14
The company reaches out to him, pays him for it, uses it,

S2 13:18
and now he has all these people hitting him up in the DMs

S2 13:21
to basically create something similar.

S2 13:23
So he was infinitely curious.

S2 13:25
He saw that like, oh wow, Bolt's just like fast growing company.

S2 13:28
I'm gonna maybe ride that wave jitter.

S2 13:30
Amazing tool. So he learned how to use jitter.

S2 13:32
He's already a good designer, right?

S2 13:33
He made the animation for free posted out there.

S2 13:36
It was sick, got noticed, and now he has tons of leads. This isn't luck.

S1 13:40
This is what happens when platforms actually align with creators.

S2 13:44
I was talking to one of our most successful users and he's like 25.

S2 13:48
He is basically saying that he learned skills by looking at contrast,

S2 13:52
seeing who's actually earning with which tools,

S2 13:54
and then learning that tool and becoming proficient.

S2 13:57
But now, like, the tools are so good.

S2 13:59
Like if you're creative and you have good ideas,

S2 14:01
like you can learn a tool and create crazy things.

S2 14:04
Like, I wish I was coming up in this in this ecosystem.

S2 14:07
It's so it's like the stuff you could do today is nuts.

S2 14:10
And now Midjourney just launched video.

S2 14:11
It's like, it's the best time ever to be a creative.

S2 14:14
It's just like some people pay attention to the noise.

S2 14:17
Some people just heads down and just like, make it happen.

S1 14:20
There's a shift happening in creative work,

S1 14:22
and Ben calls it the Hollywood model for everyone.

S2 14:25
The means of production are now available to all,

S2 14:28
and the people with the best ideas can win.

S2 14:30
So you have all of these amazing ideas

S2 14:32
and you're able to pull in these amazing collaborators.

S2 14:35
That's like the Hollywood model, right?

S2 14:36
I guess you bring together a team for a very specific outcome, right?

S2 14:39
Whether it's the UX tool survey or the yearbook project,

S2 14:42
that was the OG Hollywood model where like you get

S2 14:45
a set of like production staff

S2 14:47
and the camera crew and the director and the actors,

S2 14:50
and you all work on these different projects

S2 14:52
for these different periods of time, and then you move on.

S2 14:54
But you always work together again, and you build trust that way.

S2 14:57
You know, the way that you're operating today.

S2 14:59
Building this new like media company is the same way

S2 15:01
that I think everyone's going to operate in the future.

S2 15:04
Like you're just ahead of the curve, and culture is just trying to keep up

S2 15:07
with what all the best creatives have always been doing.

S1 15:10
Which brings me to right now.

S1 15:12
This time I'm doing it different.

S1 15:14
I'm building internet and lawyers sort of media and product studio.

S1 15:18
Same mission, hopefully new wisdom,

S1 15:21
tens of thousands of my own dollars,

S1 15:23
a team of incredible people and media that I think tech

S1 15:26
and design need and software that I want to build for me,

S1 15:30
not optimized for algorithms, not built as a funnel, but built for meaning,

S1 15:35
then went from being a college dropout to building the future of work

S1 15:39
not despite being an outsider, but because of it.

S1 15:42
The pain cave isn't where the dreams go to die,

S1 15:44
it's where they go to transform.

S1 15:45
If you're hearing this feeling like an outsider burning money

S1 15:49
on a dream that everyone else thinks is stupid, you're not alone.

S1 15:53
We're all in that pain cave and the only way out is through.

S1 15:57
Big bets are terrifying.

S1 15:58
Ben is betting on community and the new way of creative work.

S1 16:02
I'm betting on media and trying to make creative technology

S1 16:05
fun and approachable again.

S1 16:07
Follow me as I learn how to do it

S1 16:09
from some of the best in the business. See you next time!